The Definitive Reading List For Each Of Rory Gilmore's Boyfriends

Happy Gilmore Month! On November 25, our favorite mother-daughter duo returns in Netflix's Gilmore Girls: A Year in the Life. To celebrate, we're counting down until the bingefest begins, revisiting the show's best moments, debating Rory's boyfriends, and going all-out Gilmore every day for 25 days. Here, we break down Rory's reading list—boy by boy.

The Gilmore Girls Boyfriend Debate has probably run its course at this point, especially now that creator Amy Sherman-Palladino has said focusing so much on Rory's love life is really missing the point. Maybe the question we should really be asking ourselves is this: which of Rory's boyfriends provided the best reading material?

Rory was a bookworm throughout the show, and literary references were one of the major ways she bonded with her love interests – at least two of them. So let's take a look at the books that defined each of Rory's great loves.

DEAN

Netflix

There's kind of a running theme throughout a lot of these picks – they're not so much books that Rory and Dean read together, as books that Dean saw Rory reading. There's a bunch that fall into this category, but to his credit, Dean did show genuine interest in books back in season one. That faded fast once Jess was introduced, probably because the writers wanted to make him The Literary One in contrast to Dean, who basically never picked up a book again. RIP, Dean's secret literary side.

1. Moby Dick by Herman Melville

"Kind of a cliche for your first Melville," Rory acknowledges to a bemused Dean in one of their first interactions, when he spots her reading under a tree and strikes up a conversation. He also saw her reading Gustave Flaubert's Madame Bovary the week before, which would have been a way sexier choice for an opening line, but you do you, Dean.

2. A Room of One's Own by Virginia Woolf

Rory is reading Woolf's extended feminist essay as she's waiting for the bus to Chilton early in season one – and Dean ends up getting on the bus with her, despite the fact that he doesn't even go there. "Good book?" he asks. "I don't know yet," she replies, mostly because she's still crushing hard on Dean and his floppy hair and is too nervous to engage properly. If only Dean had paid a little more attention to her reading material, he might have known not to bring up the whole Donna Reed thing later in the season.

3. Anna Karenina by Leo Tolstoy

Dean did actually do some reading of his own, as became clear midway through season one when he described Tolstoy's realist classic (one of Rory's favorite books) as "depressing." But then again, Dean would think that, because he is very clearly the Count Karenin in this equation. Quick explainer if you're not up on your Tolstoy: Anna is trapped in a loveless marriage to Karenin, and strikes up an affair with a roguish young bachelor named Count Vronsky. …Yup. Can't imagine why Rory would relate.

4. Emma by Jane Austen

Soon after they start dating, Rory and Dean are doing a cute kind of cultural book exchange thing, and as he returns her copy of Emma she asks what he thought. "Well, I could tell you, but then I'd have to kill you," he says, before admitting that he liked it.

5. Fear and Loathing In Las Vegas by Hunter S Thompson

In return for agreeing to read Jane Austen, Dean tells Rory that she "has to read Hunter S Thompson," suggesting he's a fan. He doesn't mention a specific book, but let's go ahead and assume Dean hasn't got that deep into the Thompson canon just yet.

See, though? Dean had options about literature once! What happened to that? Oh, right…

JESS

This guy happened. Books were the defining thing that brought Rory and Jess together – so much so that their ship name is "Literati" in some circles – and Jess's bookishness was endearing enough to offset his major attitude problem.

1. Howl by Allen Ginsberg

In Jess's very first episode – season two's 'Nick and Nora / Sid & Nancy' – he and Luke go over to Lorelai and Rory's place for dinner, which goes exactly as well as you expect. It's during that ill-fated evening that Jess swipes a copy of Howl from Rory's bookshelf (without asking), and later returns it with annotations in the margin. Depending on what kind of bookworm you ask, this is either a swooningly romantic gesture (he wrote in her book!) or the definition of evil (he WROTE in her BOOK!).

2. Oliver Twist by Charles Dickens

Fortunately, Rory is charmed by the whole Howl incident, and affectionately calls Jess "Dodger" in response, asking him to figure out what book he's referencing. He gets the Dickens reference immediately, natch.

3. Please Kill Me: The Uncensored Oral History of Punk by Legs McNeil, Gillian McCain

Honestly, the only surprising thing about Jess's choice of reading material is that he's ever reading anything other than punk memoirs. In the episode where Rory tries valiantly to help Jess study, all he wants to talk about is this oral history of the punk movement – and he ends up lending it to Rory, whose reaction we sadly never get to hear.

4. The Fountainhead by Ayn Rand

This is one of Rory's more surprising favorites, and comes up during the episode where Jess outbids Dean for Rory's picnic basket (this qualifies as an alpha power move in Stars Hollow). As the pair share Rory's ill-prepared picnic, she reveals that she first read The Fountainhead when she was ten – but didn't understand a word, so had to re-read it five years later. Jess has never made it through the novel, which is perhaps the ultimate evidence of his good taste.

"Ayn Rand is a political nut," he points out, which, yup. Rory urges him to give The Fountainhead another chance, and he agrees, but only on the condition that she give Ernest Hemingway another chance.

5. High Fidelity by Nick Hornby

Remember when Rory briefly lost her mind and took a bus to go visit Jess in New York on the day of Lorelai's graduation? Even if this weren't logistically impossible (it's at least a three-hour ride), it would be an insane decision when she could have picked literally any other day to sneak off and see Jess. Anyway – once she's in Manhattan, Jess takes Rory to a record store that he promises is "right out of High Fidelity."

6. One Hundred Years of Solitude by Gabriel Garcia Marquez

Jess is reading Marquez's sprawling magnum opus as he hops a bus to California in pursuit of his doomed spinoff show. It's a fitting choice, since Jess is pretty much choosing solitude over community here, exiling himself from Star's Hollow and abandoning Rory without even saying goodbye. Jess was kind of the worst in this season, honestly.

Warner Bros. Television

7. The Subsect by Jess Mariano

…But he redeems himself in season six, when he shows up at Yale with a) some much-needed life advice for Rory, and b) his own actual book. Because during those couple of years when Rory was having an early-life crisis, sleeping with married men and stealing boats and jumping off scaffolding, Jess was getting his act together and writing a novel.

LOGAN

Warner Bros. Television

This came as kind of a surprise (though in retrospect it maybe shouldn't have). Logan is the least literate of Rory's boyfriends by a really, really wide margin – we were only able to come up with four memorable book references from Rory and Logan's entire relationship. Maybe this is the secret reason for the personality change Rory underwent when she started dating him. Still, here's the Logan Reading List for what it's worth…

1. A Heartbreaking Work Of Staggering Genius by Dave Eggers

Rory is reading this in her dorm room right before Logan knocks on her window in season five, and they sleep together for the first time. It's easy to imagine a post-coital conversation about the book – Logan would probably be into the flamboyant language, and considering his awful parents you know he's fantasized about being an orphan a few times.

2. My Lai 4: A Report on the Massacre and Its Aftermath by Seymour M. Hersh

Rory tells Logan in season five that she's been obsessed with Seymour M. Hersh ever since she read this chronicle of a Vietnam War incident in which hundreds of Vietnamese civilians were massacred by US Army soldiers. Rory was 12 when she read this, which seems totally normal and fine.

3. The Nancy Drew Series by Carolyn Keene

In the same episode where she reveals her Hersh obsession, Rory also tells Logan that she devoured the Nancy Drew series before moving onto the My Lai massacre.

4. The Year of Magical Thinking by Joan Didion

The season six episode in which Luke, Lorelai, Rory and Logan go on a double-date getaway to Martha's Vineyard is a low point for the entire series, mostly because of how out-of-character Luke is throughout the whole thing. But at least Rory's reading material is on point – she's reading Joan Didion's devastating memoir throughout the trip.

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